CA1134367A - Process for the preparation of tricyclazole - Google Patents
Process for the preparation of tricyclazoleInfo
- Publication number
- CA1134367A CA1134367A CA000331948A CA331948A CA1134367A CA 1134367 A CA1134367 A CA 1134367A CA 000331948 A CA000331948 A CA 000331948A CA 331948 A CA331948 A CA 331948A CA 1134367 A CA1134367 A CA 1134367A
- Authority
- CA
- Canada
- Prior art keywords
- formic acid
- tricyclazole
- reaction
- xylene
- aromatic hydrocarbon
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 238000000034 method Methods 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 68
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract description 34
- 235000019253 formic acid Nutrition 0.000 claims abstract description 34
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 11
- DYWNRVWOUASMDT-UHFFFAOYSA-N (4-methyl-1,3-benzothiazol-2-yl)hydrazine Chemical compound CC1=CC=CC2=C1N=C(NN)S2 DYWNRVWOUASMDT-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 20
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 18
- 239000008096 xylene Substances 0.000 claims description 18
- 238000004821 distillation Methods 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 14
- 239000011541 reaction mixture Substances 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 5
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 240000007594 Oryza sativa Species 0.000 abstract description 2
- 235000007164 Oryza sativa Nutrition 0.000 abstract description 2
- 235000009566 rice Nutrition 0.000 abstract description 2
- 238000010626 work up procedure Methods 0.000 abstract description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 239000012535 impurity Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- PIUXNZAIHQAHBY-UHFFFAOYSA-N 4-methyl-1,3-benzothiazole Chemical compound CC1=CC=CC2=C1N=CS2 PIUXNZAIHQAHBY-UHFFFAOYSA-N 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- SPEMKEWCLHMPRK-UHFFFAOYSA-N 1,2-bis(4-methyl-1,3-benzothiazol-2-yl)hydrazine Chemical compound N(NC=1SC2=C(N1)C(=CC=C2)C)C=2SC1=C(N2)C(=CC=C1)C SPEMKEWCLHMPRK-UHFFFAOYSA-N 0.000 description 2
- DXYYSGDWQCSKKO-UHFFFAOYSA-N 2-methylbenzothiazole Chemical compound C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JYSUYJCLUODSLN-UHFFFAOYSA-N 1,3-benzothiazol-2-ylhydrazine Chemical compound C1=CC=C2SC(NN)=NC2=C1 JYSUYJCLUODSLN-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- -1 isopropyL ester Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US93063878A | 1978-08-03 | 1978-08-03 | |
| US930,638 | 1978-08-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1134367A true CA1134367A (en) | 1982-10-26 |
Family
ID=25459558
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000331948A Expired CA1134367A (en) | 1978-08-03 | 1979-07-17 | Process for the preparation of tricyclazole |
Country Status (13)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EG17986A (en) * | 1985-08-09 | 1991-08-30 | Lilly Co Eli | Synthesis of tricyclazole |
| AU2003230185A1 (en) * | 2003-01-07 | 2004-07-29 | Indofil Chemicals Company | Industrial process for preparing environmentally safe tricyclazole |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1026341A (en) * | 1971-10-12 | 1978-02-14 | Eli Lilly And Company | Benzothiazole for controlling plant pathogenic organisms |
| BE789918A (fr) * | 1971-10-12 | 1973-04-11 | Lilly Co Eli | Benzothiazoles dans la lutte contre les organismes phytopathogenes |
| HU165912B (enrdf_load_stackoverflow) * | 1972-10-10 | 1974-12-28 |
-
1979
- 1979-07-16 IL IL57808A patent/IL57808A/xx not_active IP Right Cessation
- 1979-07-16 PH PH22785A patent/PH18848A/en unknown
- 1979-07-16 HU HU79EI872A patent/HU180743B/hu not_active IP Right Cessation
- 1979-07-17 DE DE19792928867 patent/DE2928867A1/de active Granted
- 1979-07-17 CA CA000331948A patent/CA1134367A/en not_active Expired
- 1979-07-20 FR FR7918832A patent/FR2432522A1/fr active Granted
- 1979-07-23 BR BR7904678A patent/BR7904678A/pt not_active IP Right Cessation
- 1979-07-24 GB GB79257520A patent/GB2027700B/en not_active Expired
- 1979-07-24 IT IT24615/79A patent/IT1122311B/it active
- 1979-07-26 MX MX798255U patent/MX5913E/es unknown
- 1979-07-27 ES ES482930A patent/ES482930A1/es not_active Expired
- 1979-07-27 JP JP9664379A patent/JPS5522680A/ja active Granted
- 1979-08-08 IE IE1415/79A patent/IE48382B1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB2027700B (en) | 1982-11-03 |
| GB2027700A (en) | 1980-02-27 |
| HU180743B (en) | 1983-04-29 |
| IT7924615A0 (it) | 1979-07-24 |
| BR7904678A (pt) | 1980-07-08 |
| MX5913E (es) | 1984-08-23 |
| JPS6252754B2 (enrdf_load_stackoverflow) | 1987-11-06 |
| IT1122311B (it) | 1986-04-23 |
| IL57808A0 (en) | 1979-11-30 |
| FR2432522B1 (enrdf_load_stackoverflow) | 1983-11-18 |
| IE791415L (en) | 1980-02-03 |
| DE2928867A1 (de) | 1980-02-21 |
| IL57808A (en) | 1983-06-15 |
| FR2432522A1 (fr) | 1980-02-29 |
| DE2928867C2 (enrdf_load_stackoverflow) | 1988-11-17 |
| JPS5522680A (en) | 1980-02-18 |
| PH18848A (en) | 1985-10-14 |
| IE48382B1 (en) | 1984-12-26 |
| ES482930A1 (es) | 1980-09-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |